A Highly Efficient and Stereoselective Cycloaddition of Nitrones to N-Vinylpyrroles

Alexander P. Molchanov; Ruslan S. Savinkov; Alexander V. Stepakov; Galina L. Starova; Rafael R. Kostikov; Victoriya S. Barnakova; Andrey V. Ivanov

doi:10.1055/s-0033-1340479

Synthesis, Table of Contents

Synthesis 2014; 46(06): 771-780
DOI: 10.1055/s-0033-1340479

paper

A Highly Efficient and Stereoselective Cycloaddition of Nitrones to N-Vinylpyrroles

Authors

Alexander P. Molchanov*

^aDepartment of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, 198504 Saint Petersburg, Russian Federation Fax: +7(812)4286939 Email: s.lab@pobox.spbu.ru
Ruslan S. Savinkov

^aDepartment of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, 198504 Saint Petersburg, Russian Federation Fax: +7(812)4286939 Email: s.lab@pobox.spbu.ru
Alexander V. Stepakov

^aDepartment of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, 198504 Saint Petersburg, Russian Federation Fax: +7(812)4286939 Email: s.lab@pobox.spbu.ru
Galina L. Starova

^aDepartment of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, 198504 Saint Petersburg, Russian Federation Fax: +7(812)4286939 Email: s.lab@pobox.spbu.ru
Rafael R. Kostikov

^aDepartment of Chemistry, Saint Petersburg State University, Universitetsky pr. 26, 198504 Saint Petersburg, Russian Federation Fax: +7(812)4286939 Email: s.lab@pobox.spbu.ru
Victoriya S. Barnakova

^bA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation
Andrey V. Ivanov

^bA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation

Abstract

All articles of this category

Abstract

1,3-Dipolar cycloadditions of a number of C-aryl, C-carbamoyl-, and C,C-bis(methoxycarbonyl)nitrones and substituted N-vinylpyrroles proceed with high efficiency and regioselectivity with the formation of only one isomeric substituted 5-(1H-pyrrol-1-yl)isoxazolidine cycloadduct.

Key words

pyrroles - nitrones - isoxazolidines - cycloaddition - stereoselectivity

Full Text

References

References

1a Jones RC. F, Martin JN. Synthetic Application of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products . In Chemistry of Heterocyclic Compounds. Vol. 59. Padwa A, Pearson WH. Wiley; New York: 2002: 1-81
1b Tufariello JJ In 1,3-Dipolar Cycloaddition Chemistry . Vol 2. Padwa A. Wiley; New York: 1984: 83-168
1c Torsell KB. G. Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis. VCH; Weinheim: 1988

2a Tran TQ, Diev VV, Starova GL, Gurzhiy VV, Molchanov AP. Eur. J. Org. Chem. 2012; 2054
2b Stepakov AV, Larina AG, Boitsov VM, Molchanov AP, Gurzhiy VV, Starova GL. Tetrahedron Lett. 2012; 53: 3411
2c Diev VV, Tran QT, Molchanov AP. Eur. J. Org. Chem. 2009; 525
2d Tran TQ, Diev VV, Molchanov AP. Tetrahedron 2011; 67: 2391
2e Larina AG, Stepakov AV, Boitsov VM, Molchanov AP, Gurzhiy VV, Starova GL, Lykholay AN. Tetrahedron Lett. 2011; 52: 5777
2f Molchanov AP, Tran TQ. Russ. J. Org. Chem. (Engl. Transl.) 2012; 48: 1283
2g Tran TQ, Savinkov RS, Diev VV, Starova GL, Molchanov AP. Tetrahedron 2013; 69: 5173
2h Diev VV, Stetsenko OV, Tran TQ, Kopf Y, Kostikov RR, Molchanov AP. J. Org. Chem. 2008; 73: 2396

3 Joule JA, Mills K, Smith GF. Heterocyclic Chemistry . 4th ed. Blackwell Science; Oxford: 2000
4 Sobenina LN, Tomilin DN, Ushakov IA, Mikhaleva AI, Ma JSh, Yang G, Trofimov BA. Synthesis 2013; 45: 678
5 Belyaeva KV, Andriankova LV, Nikitina LP, Ivanov AV, Afonin AV, Ushakov IA, Malkina AG, Mikhaleva AI, Trofimov BA. Synthesis 2011; 2843

6a Tedeschi RJ. Acetylene . In Encyclopedia of Physical Science and Technology, Vol. 1. 3rd ed.; Meyers RA. Academic Press; San Diego: 2001: 55-89
6b Wang Z. Comprehensive Organic Name Reactions and Reagents . Part 3 Wiley; London: 2009: 2793-2796
6c Name Reactions in Heterocyclic Chemistry II . Li JJ. Wiley-VCH; Hoboken: 2011: 72-82

7 Suitable crystals were obtained from abs EtOH. Crystallographic data for the structures 6d and 7g have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 973813 and 945026 respectively. Copies of these data can be obtained on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (e-mail: deposit@ccdc.cam.ac.uk).

8a Brandi A, Cicchi S, Cordero FM, Goti A. Chem. Rev. 2003; 103: 1213
8b Brandi A, Goti A. Chem. Rev. 1998; 98: 589
8c Goti A, Cordero FM, Brandi A. Top. Curr. Chem. 1996; 178: 1
8d Revuelta J, Cicchi S, de Meijere A, Brandi A. Eur. J. Org. Chem. 2008; 1085
8e Cardona F, Goti A, Brandi A. Eur. J. Org. Chem. 2007; 1551
8f Marradi M, Brandi A, Magull J, Schill H, de Meijere A. Eur. J. Org. Chem. 2006; 5485

9 Huisgen R, Hauck H, Grashey R, Seidl H. Chem. Ber. 1968; 101: 2568
10 Huisgen R, Hauck H, Grashey R, Seidl H. Chem. Ber. 1969; 102: 736
11 LeBel NA, Post ME, Whang JJ. J. Am. Chem. Soc. 1964; 86: 3759
12 Tice CM, Ganem B. J. Org. Chem. 1983; 48: 5048
13 DeShong P, Leginus JM. J. Am. Chem. Soc. 1983; 105: 1686
14 Es-Sayed M, Devine P, Burgess LE, de Meijere A, Meyers AI. J. Chem. Soc., Chem. Commun. 1995; 141
15 Cicchi S, Goti A, Brandi A, Guarna A, De Sarlo F. Tetrahedron Lett. 1990; 31: 3351
16 Dhavale DD, Gentilucci L, Piazza MG, Trombini C. Liebigs Ann. Chem. 1992; 1289
17 Revuelta J, Cicchi S, Brandi A. Tetrahedron Lett. 2004; 45: 8375
18 Aziza J, Font J, Ortuno RM. Tetrahedron Lett. 1991; 32: 1979
19 Chiacchio U, Corsaro A, Iannazzo D, Piperno A, Procopio A, Rescifina A, Romeo G, Romeo R. J. Org. Chem. 2002; 67: 4380
20 Iannazzo D, Brunaccini E, Giofre SV, Piperno A, Romeo G, Ronsisvalle S, Chiacchio MA, Lanza G, Chiacchio U. Eur. J. Org. Chem. 2010; 5897
21 Trofimov BA, Korostova SE, Balabanova LN, Mikhaleva AI. Russ. J. Org. Chem. (Engl. Transl.) 1978; 14: 1614

22a Gautheron-Chapoulaud V, Pandya SU, Cividino P, Masson G, Py S, Vallee Y. Synlett 2001; 1281
22b Tomioka Y, Nagahiro C, Nomura Y, Maruoka H. J. Heterocycl. Chem. 2003; 40: 121
22c Molchanov AP, Tran TQ, Kostikov RR. Russ. J. Org. Chem. (Engl. Transl.) 2011; 47: 269